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What 6 Successful Women Were Doing in Their 20s

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As a not famous “twenty-something,” I catch myself and friends looking around thinking, “Wasn’t I supposed to be somewhere by now?” Those 30 Under 30 features come around every year, and we try not to compare ourselves, or worse, flat-out panic. Of course, the more reasonable aspects of ourselves step in to remind us that we’re figuring it out and doing just fine. Still though, it’s nice to hear stories of wildly successful women who didn’t have it all together at 25.

This isn’t to say that anything will just “figure itself out” or “fall into place”—I’m not that kind of girl. The one common denominator of all these successful women is that even when they hadn’t figured it out yet, they were working their butts off. A struggling single mother on welfare was dreaming of a boy wizard, then using every spare moment to write. A future comedy legend was working at a YMCA to pay for comedy classes. So keep grinding, and fear not.

1. Suze Orman

After leaving college before finishing her bachelor’s degree in social work, Orman spent the next four years working as a waitress at a bakery in California. (On a related note, have you read The Money Book for the Young, Fabulous & Broke? The woman knows what she’s talking about.) At 26, she borrowed $52,000 from friends to open a restaurant, and she lost all of it within three months of opening. She began learning everything she could about investing and was hired by Merrill Lynch to fill their “woman quota,” despite being told that women weren’t meant to work in business. With a current net worth of about $35 million, she ended up doing alright.

[Related: 9 Things Successful People Do Right Before Bed]

2. J.K. Rowling

In her own words, the multimillionaire was “wearing heavy eyeliner, listening to the Smiths, and reading Dickens and Tolkien” in her early twenties when she went to work as a secretary for Amnesty International. By 27, she was married. By 28, she was divorced, on welfare, and struggling to take care of her daughter. Rowling has said that she saw herself as “the biggest failure I knew.” Of course, during that time she began teaching and writing in her spare time, and by 30 she finished the manuscript for Harry Potter and the Philosopher’s Stone. It was rejected by 12 publishers, until Bloomsbury finally picked it up. After that she did…moderately well.

[Related: Books from You Childhood You Should Read Again]

3. Kristen Wiig

After attending the University of Arizona as an art student, Kristen Wiig worked at a plastic surgery clinic, drawing women’s postsurgical bodies. (There had to have been some comedy potential there.) When she gathered the courage to move to L.A. to try to act, she held a series of odd jobs: working at Anthropologie, selling peaches at a farmers’ market, catering Hollywood events, babysitting, painting interiors at a floral design shop, and selling hot dogs at a mall. Oh yeah. Finally, she was introduced to the comedy troupe the Groundlings and debuted on SNL at 32.

4. Oprah Winfrey

You’ve probably heard this story before: of that poor, misguided soul who fired Oprah from her news anchor position at Baltimore’s WJZ-TV? Oprah was told she was “too emotionally involved” in the stories. She also struggled in her personal life, having a tumultuous love affair with a married man, becoming depressed, struggling with her weight, and in one relationship, experimenting with drugs. But by 31, her talk show had gone national with great success and she met Stedman, who is obviously Mr. Oprah to this day.

5. Dorothy Allison

The author of 1992 National Book Award finalist Bastard Out of Carolina, Allison held a wide variety of jobs in her 20s. She worked as a salad girl, a maid, a nanny, a substitute teacher, and a feminist bookstore clerk in Florida. She worked at a child care center, answered phones at a rape crisis center, and clerked with the Social Security Administration. At 30, Allison moved to New York and began taking classes in urban anthropology, teaching college classes, and writing. All of these experiences provided content and inspiration for her acclaimed writing career—especially her debut novel, published when she was 43 years old.

6. Tina Fey

If you’ve read Bossypants—if you haven’t why are you wasting time reading this? Go get it—you know that our favorite comedian spent some time folding towels and working at the front desk of a Chicago YMCA. Of course, this was to pay for her Second City classes, but still. Behold, the beauty of the side gig.

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Photo: Don Arnold / Getty Images

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Career Path Career Advice 20s
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Love this! Everyone thinks we need to have it all together as soon as we graduate college, and the honest (and sometimes scary) truth of the matter is that we don't. Not at all.

We can't compare ourselves to everyone else and what we they think we SHOULD be doing, but instead, if we focus on what we want and love to do, then we're already on the right path!

Great and encouraging article! I dream of the success I want but its not easy out there and you sometimes wonder how the lovely ladies above amongst others figured it out. Its a great reminder that they were once where we are. Thanks for sharing :)

Pocketing this article for a rainy day when I'm feeling below average. This is a great reminder that you're never too old - or young - to achieve your dreams. Great article!

When these women were in their 20s, it was actually possible to achieve something from nothing. No connections, no education, no network. Now you have to have the golden alignment to get a job that you should feel privileged to even have, paying you less than a living wadge.

Amen! What a great reminder and perspective on the amazingness that you can achieve at any age!

I have to say, this article was a pleasant surprise. I came in thinking: "Great. What other things am I currently not doing that would help me reach success?" It's nice to know not having your life figured out in your twenties doesn't set the course for your future.

Here I was thinking I must be doing something wrong, at 23 its impossible to have all your ducks in a row. Best thing is to stay consistent at what your passionate about and well things will play out in your favor.


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